Previous research indicates that many children have difficulty transitioning from preschool to kindergarten, which may be attributed to differences between the two settings. The purpose of this study was to investigate preschool and elementary school educators’ perceptions of the similarities of and differences between the two types of settings and their perceptions of how preschool-elementary collaborations could facilitate young children’s transition to kindergarten. Twelve early childhood educators from elementary and preschool settings were interviewed. All educators saw more differences compared to similarities between the two settings. For example, they viewed elementary school as more focused on academic domains. Educators noted that the elementary school curriculum and flow of day was generally more structured, and that preschools tended to promote greater family engagement. Participants suggested that by engaging in joint activity together, these two groups of educators could learn about each others' institutions and find ways to facilitate kindergarten transition.